This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides wherein the aryl group thereof is substituted by an amino, isocyanato, carbamate, amido, thiocarbamate or ureido group. The compounds of this invention are useful as agricultural chemicals, such as plant growth regulants and herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, discloses the preparation of compounds of the following formula and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R.sub.2 is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl. PA1 R.sub.2 is --NCO, --NHCOOR.sub.3, --NHCOSR.sub.3, --NHCOR.sub.3, --NHCONR.sub.4 R.sub.5 or --NR.sub.6 R.sub.7 ; PA1 R.sub.3 is alkyl of 1-4 carbon atoms; PA1 R.sub.4 is H or CH.sub.3 ; PA1 R.sub.5 is H, alkyl of 1-4 carbon atoms or methoxy; PA1 R.sub.6 is H or alkyl of 1-3 carbon atoms; PA1 R.sub.7 is H or alkyl of 1-3 carbon atoms; or PA1 R.sub.6 and R.sub.7 taken together are EQU --(CH.sub.2).sub.n -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA1 n is 4 or 5; PA1 R.sub.11 is alkyl of 1-3 carbon atoms; PA1 m is 0 or 2; PA1 X is methyl, methoxy or ethoxy; PA1 Y is methyl or methoxy; and PA1 Z is CH or N; PA1 (a) when R.sub.2 is ortho to the sulfonylureido group, then R.sub.1 must be hydrogen and R.sub.2 cannot --NCO; PA1 (b) when R.sub.5 is methoxy, R.sub.4 is methyl; PA1 (c) when R.sub.2 is --NCO, the compound cannot be a salt; and PA1 (d) when R.sub.2 is --NCO, --NHCOOR.sub.3 or --NHCONR.sub.4 R.sub.5 and Z is nitrogen, then R.sub.1 must be alkyl of 2-4 carbon atoms or R.sub.11 S(O).sub.m. PA1 R.sub.2 is --NR.sub.6 R.sub.7, --NCO, --NHCOOCH.sub.3, --NHCOCH.sub.3 or --NHCON(CH.sub.3).sub.2 ; and PA1 R.sub.6 and R.sub.7 are independently hydrogen or alkyl of 1-3 carbon atoms. PA1 R.sub.1 is alkyl of 2-3 carbon atoms or R.sub.11 S(O).sub.m. PA1 R.sub.2 is --NR.sub.6 R.sub.7 or --NCO; PA1 R.sub.6 and R.sub.7 are independently hydrogen or methyl; and PA1 X is methyl or methoxy. PA1 R.sub.1 is hydrogen, chlorine, methyl or methoxy.
U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R.sub.1 is hydrogen or lower saturated aliphatic acyl; and
The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=halogen, CF.sub.3 or alkyl.
Compounds of the following formula, and their use as antidiabetic agents, are reported in J. Drug Res. 6. 123 (1974): ##STR4## wherein R is pyridyl.
Logemann et al., Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR5## wherein R is butyl, phenyl or ##STR6## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Argentine Pat. No. 174,510 (attached hereto) teaches compounds of the general formula: ##STR7## In this formula R.sup.1, R.sup.2 and R.sup.3 are equal or different and represent hydrogen or alkyl or alkenyl groups which can also be substituted for example by --OH, --Cl, --SH, --NO.sub.2 or --NH.sub.2 groups. The radicals R.sup.1 and R.sup.2 can also be closed in the form of a five- or six-membered ring. R.sup.4 represents hydrogen or an alkyl or aryl radical which can also be substituted. Between the group X and the radical R.sup.4 there can also be an SO.sub.2 group. X represents a bridge of oxygen, nitrogen or sulfur, which connects the CO group with a radical R.sup.4. Y is an atom of chlorine or the radical --CH.sub.3, --CH.sub.2 Cl, --CHCl.sub.2 or CCl.sub.3.
Wojciechowski, J. Acta. Polon. 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR8## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Substituted pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR9## where R=H or CH.sub.3.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation are available; such materials are commonly referred to as herbicides. However, the need still exists for effective herbicides that destroy or control weeds while not significantly damaging useful crops. Some weeds (nutsedge is a particular example) are very difficult to control; many of the herbicides that are used to control nutsedge are so nonselective that they cause damage to the crops themselves.